Life's Undress Rehearsal
by eclecticxdetour
Summary: [WINCEST of the SamDean Persuasion][Rated M for Extreme SLASH][Sam is 17, Dean is 21]After the SATs Dean takes Sam to Target for some new clothes, leaving with more than they'd ever thought they'd have together.


"How do you think you did, Kid?" asked Dean, fixing the rear-view mirror of the Impala as Sam climbed in next to him.

"I'm seventeen years old, Dean, I think that qualifies me as an adult now," replied Sam, not bothering to answer Dean's question.

Dean scoffed as he elbowed Sam in the side, pulling out of the high school parking lot, "You're still four years younger than me, which still qualifies you as my kid brother, so I'll call you kid if I damn well please, Sammy. And, you're not an adult until you're eighteen, genius."

Sam rolled his eyes and tucked his knees up against the dashboard, leaning his forehead up against the window as he shrugged, answering Dean's question, "I Think I did well."

Dean spared a glance at Sam as they merged onto the main road, "Oh yeah?"

Sam looked to Dean and nodded, "Uh-huh. Critical Reading and Writing were easy as pie, and the math wasn't terrible this time 'round."

Dean grinned at Sam and patted his brother's knee, "That's good to hear."

"Yeah," sighed Sam, then his brow wrinkled in a frown, "Dean, this isn't the way back to the house, man."

"I know, Sammy. Need to go to Target and buy some more long sleeved shirts; that bitch of a spirit fucked up the lot of ours on the last hunt." He fingered the hole at the knee of Sam's jeans and muttered, "Should probably buy you a couple pairs of new jeans, too."

Sam nodded in understanding and then perked up at the idea of food as his stomach gave a rumble, "Think you can get me a Churro and a Caramel Chillatta at the Cinnabon along with the clothes?"

They pulled up at a stop light and Dean quirked a brow at his brother, "A Caramel Chill-whatta?"

"Chillatta," said Sam, the word easily slipping off his tongue.

Dean felt an odd sort of pull low in his belly as he watched Sam's tongue form the 'la' sound in Chillatta. He cleared his throat and with one last pull to the hole in Sam's pants he returned his attention to the road, "What the hell is a Chillatta?"

Sam pursed his lips and said, "I'm not exactly sure, but they're tasty as hell and they've got lots of caramel."

Dean let out a short laugh, "Sounds like a girly drink to me."

"Fuck you," laughed Sam in turn, "I just sat through four and a half hours of testing. I think you can forgive the girliness of the drink and be a good older brother and buy one for your baby brother."

Dean rubbed his knuckles gently into Sam's skull and said, "Sure can."

Sam batted at Dean's hands and huffed as he tried to get his messy hair back into place, "Jerk."

Dean smirked, "Bitch."

"Order it for me," whispered Sam as they made their way to the Cinnabon by the movie theater.

"Hell no, Sammy. I'll pay for it, sure, but I ain't gonna order it for you."

Sam implored his Patented Sammy Look at Dean and Dean rolled his eyes and caved, shoving Sam out of the way of the Cinnabon booth and waiting to be serviced.

"Yeah, please, can I get a--" Dean glanced back at Sam and glared at him when his brother made a 'carry on' motion with his hand. Dean lowered his voice and continued, "A Caramel Chillatta and a churro?"

The young lady punched in his order and said, "$4.05."

Dean handed over a five dollar bill and the girl thanked him before putting it into the register. Dean waved Sam over to wait for his drink and his treat and he moved to stand aside. He grinned as he watched Sam shove his hands in his jeans pockets and rock back and forth on the balls of his feet. His brother could be such a geek sometimes, but hell, Dean loved him because of it.

Sam smiled hugely at the young lady and thanked her again before stepping toward Dean. He took a long swallow of his Chillatta and grinned at Dean with caramel sticky lips.

Dean rolled his eyes and snatched up a napkin from the top of the trash receptacle container and tossed it at Sam, whom juggled his Chillatta and his churro and caught the napkin with one hand.

"Alright, Geek Boy," Dean patted Sam on the chest and brushed past him, "let's get us some clothes."

Sam happily sipped his Caramel Chillatta as he trailed after Dean while his brother grabbed plaid long sleeved shirts and threw them over his arm, grabbing a few packages of black and grey t-shirts and a few pairs of jeans.

Dean looked over the clothes in his arms and hooked his arm through Sam's and hauled Sam into the dressing room with a cut off "What the fu--" from his baby brother.

Dean dumped the clothes onto the small bench attached to the wall and ran a hand through his short hair. He shrugged off his leather jacket and tossed it onto the bench next to his brother.

Sam set his Caramel Chillatta on the bench as well and stood up, pushing at Dean's shoulders as he asked incredulously, "Dude, why the hell did you shove me in the dressing room?"

Dean looked at his brother like he was stupid and said, "Because we need to try on the jeans, dumbass, duh."

Sam huffed and started working on the thick leather belt threaded through his jeans as he mumbled, "Could've got separate dressing rooms."

Dean hopped on one foot as he tried to release his trapped foot from his pant leg, "The others were occupied, Sammy, and I didn't feel like waiting around. Just wanna get in here then get out. S'that alright with you, sweetheart?"

"Don't patronize me, Dean," sniped Sam, letting his jeans drop to his ankles.

Dean couldn't help the way his eyes dropped down to the soft swell of Sam's cock in his tight-fitting boxer briefs.

Sam pulled his shirt over his head and shoved at Dean's shoulder as he caught his brother staring at him. He flushed from his collarbone up to his ears and crossed an arm over his crotch as he pulled a pair of jeans up his legs and he squeaked, "Quit perving on me, man, it's weirding me out."

Dean pulled his gaze away from appreciating Sam's body and looked at his brother's face, "Sorry, man. Just – wow. When the fuck didya' get those muscles, baby boy?" _'And when did your cock get so damn huge?' _supplied Dean's brain.

Sam saw Dean's eyes flicker to his groin again and he hurriedly zipped up and buttoned the jeans before tugging a shirt over his head. "Well, Dad's not making us train and spar so much for nothing, stupid."

Dean punched at Sam's arm as he tried on his own jeans and shirt, "Shut the hell up, bitch, I won't take that attitude from you."

Sam rubbed at his arm as he kicked off the jeans and pulled on his own. He ignored Dean's comment and asked, gesturing to the jeans, "All the ones you grabbed for me the same size?"

"No," grunted Dean as he tugged his pair of jeans off, "I couldn't find more than a pair of the same brands so they're all different brands and so the sizes'll be different."

"Perfect," muttered Sam, already taking his jeans of so he could try on another pair of denims.

Dean froze with the jeans mid-way down his thighs as he watched the way Sam's biceps and quads flexed as he changed. He got caught watching again and Sam smacked him upside the head.

"Seriously, man, _what the hell?_"

Dean shrugged and grabbed Sam's Chillatta so he wouldn't have to answer Sam's query. He didn't know why but his eyes kept gravitating to the gorgeously toned and built muscle--_'and oh Holy Hell, when did I start thinking of Sam as gorgeous?' _thought Dean, shaking his head as he placed the caramel drink back on the bench.

Dean finally shrugged as he managed, "Ain't got nowhere else to look, Sammy."

"Yeah? Well, that's true. But quit fucking _leering _at me, man," Sam cleared his throat as Dean wrestled his way out of his jeans, trying not to pay attention to how Dean's ass looked as he bent down, "it's--" he cleared his throat again and whispered, raising his eyes from Dean's butt, "weird."

Dean cocked an eyebrow at Sam and said, "Dude, I'm sorry. I was just spacing, man, Wasn't staring at you or anything."

Dean frowned when Sam looked to his feet, almost as if he were disappointed that he _hadn't _been looking at him with want in his ey-- _'and Goddamn it when the hell did I start thinking like a fucking cheesy romance novel?'_

Sam let out a sigh and raised his eyes back to Dean's face; he wasn't sure what he saw in his brother's eyes, but when he met Dean's gaze he felt a stirring low in his gut and just south of his belly as well.

'_Fuck,' _thought Sam, swallowing hard when Dean smoothed his hands down the blue and grey plaid shirt he'd just put on.

Sam swallowed again and froze when Dean looked at him, his head tilted to the side as he tried to figure out what was going on with Sam.

"Dude, seriously, I wasn't looking at you." _'Liar.'_

Sam waited a second, swallowing again before he thought _'Fuck it. Might as well see what happens anyway.'_

Sam dropped his hands before him, fingers fiddling with the sleeve of his own plaid shirt. He looked up at Dean through his bangs and whispered, "What if I said I _wanted _you to be looking at me?"

The jeans Dean had been holding fell from his hands as he looked incredulously at his brother, "What did you say?"

Sam blushed, taking Dean's incredulity as anger, and shook his head, holding his hands in front of him in a form of defense, "Nothing, De, just forget it."

"No, Sammy," Dean gently wrapped his fingers around Sam's wrist and tugged Sam closer to him, tilting his head up to meet his eyes, "Tell me."

Sam looked at Dean's fingers wrapped around his wrist and muttered, "I said 'What if I said I _wanted _you to be looking at me?" and then he met Dean's eyes, gasping at the intensity he saw there.

Before Sam could apologize or refute that he'd said anything at all Dean was pushing him against the wall of the dressing stall with a hard thump and his lips were on his, all wet and soft and _'Sweet Jesus, Dean's tongue is in my mouth!'_

Sam moaned quietly against Dean's mouth and settled one of his hands beneath the waistband of Dean's open jeans, fingers curling around his hip.

Dean groaned in response and pulled away from Sam, fingers playing at the clasp of Sam's jeans. "Sammy?" he asked, the two syllables of his brother's name weighted down with the _'Are you sure?'_s and the _'Is this okay?'_s and the _'Please want this too'_s.

"Yeah, De, yeah," breathed Sam, pulling Dean closer so that their bodies were flush together, aligned from chest to hip, Dean's muscular thigh pressed between his legs.

Dean captured Sam's lips again, tongue tentatively licking over Sam's bottom lip before he placed a small kiss to the corner of Sam's mouth. He opened his eyes and met Sam's in a silent question, _'Can I kiss you again?'_

Sam nodded fervently and gasped as Dean shifted his leg between his own and Dean's tongue glided into his mouth, practically sashaying against his own as his brother kissed him.

Dean didn't know what to do with his hands, it wasn't as if Sam were a girl, he couldn't just grasp onto Sam's chest like he did a chick's tits. _'I'm making out with _Sammy _for fuck's sake!' _he thought, settling his hands on Sam's hips as he shifted his leg back and forth along Sam's crotch as he continued to precariously map out Sam's mouth.

Sam groaned, rocking his hips against Dean's thigh as he raised one of his hands up to hold onto Dean's jaw, angling his head to the side so that he could take over the kiss, pushing against Dean's tongue until Dean relented and allowed Sam into his mouth, giving him his turn to explore.

Sam pulled away with a soft exhale of breath and he tossed his head back against the stall wall when Dean mouthed at the hollow of his throat, fingers sliding up his chest to pinch at a nipple.

"_Dean_," he moaned, clutching tight to Dean's hip, "Can we? I want to--"

"Yeah, Sammy. _Fuck_. Me, too," replied Dean already pushing Sam's jeans and boxer-briefs down his hips as Sam followed his lead, pushing his half-done jeans and underwear down his legs, letting them pool around his feet.

Dean groaned at the sight of Sam's cock, hard and curling toward his belly, leaking in anticipation of the attention it was going to receive. "Well _shit_, Sammy," commented Dean, eyes widening at the sheer size of Sam's cock, fingers itching to take a hold of him.

Sam blushed and finally let his eyes pan up Dean's legs and focus on Dean. His breath hitched. Dean's dick wasn't as long as his own, but _holy hell _his brother's cock was thick and dripping with pre-come and Sam just wanted to take him into his mouth and give his brother's cock all the attention that it deserved.

"Fucking perfect," murmured Sam, unable to take his eyes away from the spectacle that was Dean's erection.

Dean smirked and said, "Why thank ya', Sammy." He took in Sam's cock again and let his fingers brush against it, relishing in Sam's shiver against him, "Guess impressive cocks is hereditary down the Winchester line."

"_Man_," whined Sam, their father making his way into his head, "I really needed to think of _Dad's _junk right now, Dean, thanks."

Dean smirked again and wrapped calloused fingers around Sam's cock. He kissed Sam quickly and whispered against his brother's lips, "Don't worry, Sammy, this'll take your mind off of him. Promise."

And with Dean's first stroke Sam felt as if his knees were going to buckle out from under him. He'd never felt such pleasure before as he had in that moment. Not even when Danni'd gone done on him at junior prom.

"Really, Sammy?" asked Dean, clearly amused.

"Shit," gasped Sam when Dean thumbed the head of his cock. He thrust into Dean's grip and groaned, "Did I say that out loud?"

"Oh yeah, little brother," laughed Dean, biting Sam's jaw, "that girl, man. That one had a mouth on her, I'll tell ya'."

"Bastard," whispered Sam, fucking into Dean's fist, "you were with her?"

"Mhm," hummed Dean, "had to test drive her before I let her have at you, man."

"Don't care, De, just--" Sam's grunt cut off his words, "just keep doing what you're doin' and I'll let it slide."

"You're lettin' it slide alright," laughed Dean quietly, eyes moving from Sam's face to watch Sam's cock slip-sliding through his fist.

Sam looked down, too, and he felt absolutely useless just thrusting into his brother's fist, Dean's dick angry-looking and neglected. He quickly remedied that and palmed the crown of Dean's erection, lubricating his palm with precome before he closed his fist around Dean.

"Christ, Sammy," gasped Dean, fingers on Sam's cock faltering as he shivered from Sam's touch.

"God, Dean, can barely get my hand around you," huffed Sam, leaning his forehead against the crook of Dean's neck as he watched their hands moving along each others' turgid flesh.

Dean moaned quietly when Sam tightened his fingers around him, "_Fine_, Sammy. Here, hang on."

With some careful maneuvering Sam and Dean got their pants and underwear from around their ankles and Sam slumped against the wall of the dressing room so his groin was level with Dean's.

Dean stood between Sam's spread legs and braced his hands either side of Sam's head, Sam's hands holding onto his hips. He leant forward, whole body pressing against Sam's as he pressed their mouths together, cocks rubbing causing Sam and Dean to exchange moans.

Dean rocked on his heels, cock riding along Sam's as he thrust against his brother. He broke away from Sam's mouth and licked the shell of Sam's ear before he asked, "Better, baby boy?"

Sam nodded his head and keened, nails digging crescent-moon shapes into Dean's hips, "Yeah, De. Lot better. _Fuck_."

Dean gasped when Sam's hands found their way from his hips to his ass, fingers clutching at the muscular globes, kneading and massaging his cheeks, bringing him forward faster and harder against Sam's erection.

Sam thumped his head back against the wall of the dressing room again and let out a groan, biting down on his lower lip so as to mute his pleasure.

Dean grinned as he watched Sam try to contain himself. He bent forward so he could tongue at Sam's nipple and Sam was unable to keep to himself at the sensation of Dean's mouth hot and wet around the sensitive bud.

Dean laughed wickedly and Sam bit his shoulder.

"Aw, should've begged you for a biter, you weirdo," laughed Dean, rubbing his chin against the bruise forming on his shoulder.

"Made me moan like a bitch," pouted Sam, fingers inching their way closer to the crease of Dean's ass.

"S'cuz you are a bitch," said Dean, smirking against Sam's neck.

"Oh, I'm the bitch?" asked Sam, pitch low as he teased his fingers along Dean's crack.

Dean's eyes widened and he gasped into the juncture between Sam's neck and shoulder when he felt one of Sam's long fingers pressing gently against his hole. He pressed wantonly back against Sam's digit and moaned and shuddered when the tip of Sam's finger slipped inside.

"Oh _God_."

It was Sam's turn to grin as he rocked his hips against Dean when Dean continued pressing back against his finger and no longer thrusting into him.

"Want my finger in you, Dean?" asked Sam, mouth hovering hot and damp near Dean's ear.

A shiver wracked through Dean's body and he managed a slight nod and a shaky, "Yes."

Sam grinned wickedly and pulled his finger away from Dean's body and presented his middle finger before Dean's mouth, "Suck it."

Dean's eye shimmered with glee and anticipation and he enthusiastically sucked up Sam's finger into his mouth, tonguing his finger and sucking like he was going to do to Sam's cock at another time. Dean bit at Sam's finger when he felt his brother's finger was thoroughly slick and Sam pulled his finger away, kissing Dean like he was dying as he pressed his finger back to Dean's entrance.

"Is it gonna hurt?" whispered Sam, genuinely worried about hurting Dean.

Dean smiled, assuring, and cupped Sam's cheek, "Just a bit of a burn at first, Sammy, but it'll get better; won't hurt me, little brother." He kissed Sam, just a loving press of lips and finished, "I want it."

That was all that Sam needed to hear before he pressed gently but firmly inside, watching Dean's face for any signs of discomfort.

Dean wriggled against the intrusion, trying to concentrate on anything but the feel of Sam's finger burning its way into his body. He thrust back against Sam's finger and then forward against Sam's cock, moaning when Sam twitched against him.

Sam combed his fingers through Dean's short hair, "Alright?"

"Yeah," Dean cleared his throat, "Yeah, Sammy, m'good, now just… fuck me."

Those two words out of Dean's mouth almost had Sam coming right at that instant. "Jesus, Dean," he groaned taking a deep breath so as to keep at it just a little longer, long enough for his finger in Dean's ass to be worth some pleasure to his brother.

He swirled his finger around inside of Dean, digit slipping just that much deeper into Dean before the tip prodded against a spongy bundle. Curious, Sam scratched his nail against it and the result amazed him.

Dean's eyes widened and he buried his face in Sam's neck, biting on the smooth skin so as to muffle the shout that he wanted to let out at Sam fingering his prostate.

Sam pressed against it again and he got the same reaction out of his brother. "De? You okay there, man?"

"Fuck yes, Sam. It's--" and Sam's finger rubbed against that spot once more and Dean let out a very indignant squeak, "_Shit_."

"What _is _this?" asked Sam, wanting to know what he was touching that made his brother's body jolt with pleasure.

"P-prostate, Sammy," whimpered Dean, thrusting back and forth between Sam's finger and his cock.

"Right," said Sam, a wide grin splitting his face.

Another prod and Dean knew he was gonna come in no time at all. He grabbed a hold of Sam's cock and his own and stroked in time with the strokes of Sam's finger inside of him.

"_Dean_," Sam keened, forehead pressing against Dean's collarbone.

"C'mon, Sammy, wanna get you there."

Sam whimpered pitifully and pressed his finger hard against that spot inside Dean, holding his finger there and gasping as Dean's body went rigid against his, cock leaking copious amounts of precome over his own dick. He held on tight to Dean's asscheek and groaned against his brother's neck as he found his release, thrusting into the light grip Dean had on their cocks as he spilled hot and wet over Dean's hand and his brother's dick.

The feel of Sam's come warm and thick over his cock and fingers and the insistent press of Sam's finger against his prostate had Dean coming not two seconds after Sam, whole body slumping against his little brother's larger frame as he shuddered through his release.

Sam smiled and pressed dry lips to Dean's forehead, "Holy _fuck_, Dean."

"Yeah, Sammy, I know," agreed Dean; absolutely certain that was the best orgasm of either of their lives.

They managed to clean themselves up--Sam ready to go at it again when Dean licked their come from his fingers--and managed to look semi-presentable; Sam's sex ruffled hair deemed passable as normal by Dean's standards.

Dean snatched up their clothes and Sam grabbed his Chillata, Dean sneaking a kiss before they stepped out of the dressing room.

A young man was standing outside, mouth agape as Sam and Dean stepped in front of them. Sam blushed furiously and took a long gulp of his Chillata, leaving Dean to explain the noise away.

Dean took one glance at the kid and noticed the obvious bulge in the kid's pants. Sam walked away quickly not waiting for him to shoo the kid away and Dean finally managed, a tilt of his head in Sam's direction as he leant in close to the boy's ear, Dean laughed, "It's the Chillatas; Sammy over there says they're orgasmic."


End file.
